I had the time yesterday with the site being down all day to give this a go.

Good News: It worked and I have Apache 2.4.29 with LibreSSL 2.6.2 both x86 & x64.Bad News: I cannot find my package creating script at the moment so I have to get out my old laptop and dig through it to get it back.

Once I find it I'll package these up and make them available for download and announce. I hope I do not have to recreate my packaging script but if I do, it may take a couple days to get these up.

Is anyone else getting this message "C:/Apache/conf/httpd.conf: Cannot load modules/mod_ssl.so into server: The specified module could not be found." when they install and attempt to run Apache 2.4.29 w/LibreSSL 2.6.2?

Well this is an Apache Directive that notes OpenSSL 1.0.2 and higher. So with that in mind;

If the directive works on 2.4.29/Libressl 2.5.5, chances are whatever part of LRE's API was removed by LRE that supports this Apache directive. This would not be a surprise since there is a slimming down of the library of "unneeded code" so they deem almost every release.

Or

If the directive doesn't work on 2.4.29/Libressl 2.5.5, it's probably because LRE was forked from OpenSSL 1.0.1 and what of OpenSSL 1.0.2 is needed for the directive has never been added to LRE.